O-acetyldelectine — A new alkaloid from Delphinium dictyocarpum

9. 10. 11. S. Kh. Maekh. V. G. Khodzhaev, and S. Yu. Yunusov, Khim. P r i r o d n . Soedin., 381 (1971). M . P . Cava, V. Watanabe, K. Bessho, M. L. Mitchell, T e t r a h e d r o n Lett., 2427 (1968). H . G . Kiryakov and P. Panov, Dokl. Bolg. Akad. Nauk, 222, 1019 (1969). O-ACETYLDELECTINE FROM Delphinium -A NEW ALKALOID dictyocarpum UDC 547.944/945 B. T. Salimov, M. S. Y u n u s o v , a n d S. Y u . Y u n u s o v • Continuing the separation of the combined alkaloids of the epigeal p a r t of Delphinium dictyocarpum DC., collected in the flowering phase in the environs of the village of Topolevsky (Dzhungarian Ala-tau) [1-3], w e have isolated a new base (I), C33H46OoNz, mp 118-120°C (methanol), M+ 614. , The IR s p e c t r u m of (I) shows absorption bands at (cm -t) 3460 (hydroxy groups), 1690, 1740 (carbonyl groups), 1593 ( a r o m a t i c ring), and 1090 (ether C - O bonds). The NMR s p e c t r a has the signals corresponding to a N-ethyl group ( t h r e e - p r o t o n t r i p l e t at 1.04 ppm), an acetyl group ( t h r e e - p r o t o n singlet at 2.02 ppm), t h r e e methoxy groups ( t h r e e - p r o t o n singlets at 3.18, 3.26, and 3.2 9ppm), and four a r o m a t i c protons (multiplets at 6.61 and 7.76 ppm). The composition and s p e c t r a l c h a r a c t e r i s t i c s p e r m i t (I) to be assigned to the diterpene alkaloids with a lycoctonine skeleton. Identity of the signals of the a r o m a t i c protons in the NMR s p e c t r u m of (I) with those in t h e s p e c t r u m of delectine (II) and the p r e s e n c e of intense peak of an ion with m / e 120 in the m a s s s p e c t r u m of (I) due to an anthranilic acid residue show that the amino alcohol in (I) is acylated with anthranilic and acetic a c i d s . In the NMR s p e c t r u m of (I) at 4.73 ppm t h e r e is a o n e - p r o t o n t r i p l e t with J ~ 5 tIz. The splitting constant and the chemical shift a r e c h a r a c t e r i s t i c for a fl proton at C10 geminal to an acetoxy group [4]. According to the m a s s s p e c t r u m (in which the maximum peak is that of the ion M - 31), t h e r e is a ~ methoxy group at Ct [5]. On the basis of what has been said, it may be a s s u m e d that (I) is 10-O-acetyldelectine. To confirm this, we acetylated (I) with a c e t i c anhydride in pyridine and obtained the monoacetate (HI), CasH48OIoN2, m p 128-130°C ( h e x a n e - e t h e r ) , which was identical with the N,O-diacetate of delectine. Consequently, the new base that we have isolated has the s t r u c t u r e (I): OGH3 j~. ,,OGH~ I. R = anthranoyl Rt = COCH~ II. R = anthranoyl R, = H I11. R =acetylanthoranoyl R~=COCI% OR I LITERATURE 1= 2. 3. 4. 5. CITED A. S. Narzullaev, M. S. Yunusov, and S. Yu. Yunusov, Khim. P r i r o d n . Soedin., 498 (1972). B. T. Salimov, M. S. Yunusov, S. Yu. Yunusov, and A. S. Narzullaev, Khim. P r i r o d n . Soedin., 665 (1975). B. T. Salimov, M. S. Yunusov, and S. Yu. Yunusov, Khim. P r i r o d n . , Soedin., 128 (1977). S. W. P e I l e t i e r , L. H. Keith, and 1% C. P a r t h a s a r a t h y , J. Am. Chem. Soc., 89, 4146 (1967). M. S. Yunusov, Ya. V. Rashkes, and S. Yu. Yunusov, Khim. P r i r o d n . Soedin., 85 (1972). Institute of the C h e m i s t r y of Plant Substances, Academy of Sciences of the Uzbek SSR, Tashkent. T r a n s l a t e d f r o m Khimiya P r i r o d n y k h Soedinenii, No. 5, pp. 716-717, S e p t e m b e r - O c t o b e r , 1977. Original a r t i c l e submitted May 10, 1977. 0009-3130/77/1305- 0603507.50 © 1978 Plenum Publishing Corporation 603  (...truncated)